MiMeDB: Showing metabocard for 3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid (MMDBc0033510)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:51:37 UTC

Update Date

2024-04-30 20:11:11 UTC

Metabolite ID

MMDBc0033510

Metabolite Identification

Common Name

3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid

Description

3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid is found in alcoholic beverages. 3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid is present in soy and worcester sauces, yeast extract and wine as the (3S)-diastereoisomers. 3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid is formed by Pictet-Spengler condensation of tryptophan with 4-oxobutanoic acid to give predominantly the cis-isomer

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0034881
     RDKit          3D
3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.4394   -3.1982   -1.6431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -2.0411   -1.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -1.0255   -1.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030   -1.8099   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -0.3585    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    0.0340    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    1.4123    1.4751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    2.3337    1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    3.5079    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514    3.5229    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    4.5914   -0.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904    1.8642   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    0.4430    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.4202    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733   -1.6272    0.7719 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -1.5371    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -2.5063    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -2.1399   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496   -0.8317   -0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2836    0.1279   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0831   -0.2297   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954   -1.0613   -2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215   -2.0326   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -2.4220    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.1428    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1569    0.2679   -0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -0.5261    2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896    1.7486    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585    2.7473    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    5.1400    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.0151   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    2.4682    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -2.5295    1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -3.5440    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -2.8736   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1829   -0.5275   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    1.1604   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
 21 13  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END


  Mrv0541 02241217522D          

 21 23  0  0  0  0            999 V2000
   -2.8068    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796    0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3755    0.4129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3755    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7149    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068    1.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    2.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3755   -1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3755   -2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -2.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -2.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033510

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N2O4/c18-13(19)6-5-11-14-9(7-12(16-11)15(20)21)8-3-1-2-4-10(8)17-14/h1-4,11-12,16-17H,5-7H2,(H,18,19)(H,20,21)

> <INCHI_KEY>
PPKGNUKJFFAWHY-UHFFFAOYSA-N

> <FORMULA>
C15H16N2O4

> <MOLECULAR_WEIGHT>
288.2985

> <EXACT_MASS>
288.11100701

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.992093725186994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2-carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-1.1603111031783109

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.471828699372392

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7519168985713742

> <JCHEM_PKA_STRONGEST_BASIC>
9.309218485789424

> <JCHEM_POLAR_SURFACE_AREA>
102.42000000000002

> <JCHEM_REFRACTIVITY>
74.6187

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2-carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034881
     RDKit          3D
3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.4394   -3.1982   -1.6431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -2.0411   -1.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -1.0255   -1.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030   -1.8099   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -0.3585    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    0.0340    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    1.4123    1.4751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    2.3337    1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    3.5079    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514    3.5229    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    4.5914   -0.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904    1.8642   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    0.4430    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.4202    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733   -1.6272    0.7719 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -1.5371    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -2.5063    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -2.1399   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496   -0.8317   -0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2836    0.1279   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0831   -0.2297   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954   -1.0613   -2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215   -2.0326   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -2.4220    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.1428    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1569    0.2679   -0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -0.5261    2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896    1.7486    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585    2.7473    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    5.1400    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.0151   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    2.4682    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -2.5295    1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -3.5440    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -2.8736   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1829   -0.5275   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    1.1604   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
 21 13  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.239   2.312   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.239   0.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.906   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.575   0.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.575   2.312   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.906   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.096   2.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.096   0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.237   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.568   0.771   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.568   2.312   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.237   3.080   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.334   0.000   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.904   3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.239   2.312   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.904   4.624   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.237  -1.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.568  -2.312   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.568  -3.853   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.904  -4.624   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.237  -4.624   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12    7   11                                                       
CONECT   13    4    8                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034881
HETATM    1  O1  UNL     1      -3.439  -3.198  -1.643  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.282  -2.041  -1.189  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.107  -1.026  -1.645  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.203  -1.810  -0.171  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.247  -0.358   0.184  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.207   0.034   1.214  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.333   1.412   1.475  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.406   2.334   1.016  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.103   3.508   0.436  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.351   3.523   0.432  1.00  0.00           O  
HETATM   11  O4  UNL     1      -0.425   4.591  -0.102  1.00  0.00           O  
HETATM   12  C7  UNL     1       0.590   1.864  -0.003  1.00  0.00           C  
HETATM   13  C8  UNL     1       0.954   0.443   0.166  1.00  0.00           C  
HETATM   14  C9  UNL     1       0.090  -0.420   0.748  1.00  0.00           C  
HETATM   15  N2  UNL     1       0.673  -1.627   0.772  1.00  0.00           N  
HETATM   16  C10 UNL     1       1.899  -1.537   0.210  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.873  -2.506   0.006  1.00  0.00           C  
HETATM   18  C12 UNL     1       4.055  -2.140  -0.601  1.00  0.00           C  
HETATM   19  C13 UNL     1       4.250  -0.832  -0.991  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.284   0.128  -0.789  1.00  0.00           C  
HETATM   21  C15 UNL     1       2.083  -0.230  -0.176  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.395  -1.061  -2.625  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.221  -2.033  -0.640  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.421  -2.422   0.705  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.289  -0.143   0.560  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.157   0.268  -0.740  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.485  -0.526   2.155  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.290   1.749   1.683  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.159   2.747   1.907  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.228   5.140   0.442  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.242   2.015  -1.044  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.512   2.468   0.127  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.291  -2.529   1.151  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.723  -3.544   0.314  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.853  -2.874  -0.782  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.183  -0.528  -1.474  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.420   1.160  -1.089  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   14   27
CONECT    7    8   28
CONECT    8    9   12   29
CONECT    9   10   10   11
CONECT   11   30
CONECT   12   13   31   32
CONECT   13   14   14   21
CONECT   14   15
CONECT   15   16   33
CONECT   16   17   17   21
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   19   20   36
CONECT   20   21   21   37
END

HMDB0034881
     RDKit          3D
3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.4394   -3.1982   -1.6431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -2.0411   -1.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -1.0255   -1.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030   -1.8099   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -0.3585    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    0.0340    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    1.4123    1.4751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    2.3337    1.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    3.5079    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514    3.5229    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    4.5914   -0.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904    1.8642   -0.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    0.4430    0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.4202    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733   -1.6272    0.7719 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -1.5371    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -2.5063    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -2.1399   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496   -0.8317   -0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2836    0.1279   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0831   -0.2297   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954   -1.0613   -2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215   -2.0326   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -2.4220    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.1428    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1569    0.2679   -0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -0.5261    2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896    1.7486    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585    2.7473    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    5.1400    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.0151   -1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    2.4682    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912   -2.5295    1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -3.5440    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -2.8736   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1829   -0.5275   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    1.1604   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
 21 13  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

Synonyms

Value	Source
3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoate	Generator
1-(2-Carboxyethyl)-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid	HMDB
1-(2-Carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate	Generator

Molecular Formula

C₁₅H₁₆N₂O₄

Average Mass

288.2985

Monoisotopic Mass

288.11100701

IUPAC Name

1-(2-carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

1-(2-carboxyethyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O

InChI Identifier

InChI=1S/C15H16N2O4/c18-13(19)6-5-11-14-9(7-12(16-11)15(20)21)8-3-1-2-4-10(8)17-14/h1-4,11-12,16-17H,5-7H2,(H,18,19)(H,20,21)

InChI Key

PPKGNUKJFFAWHY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-1.2	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.75	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.62 m³·mol⁻¹	ChemAxon
Polarizability	29.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-3690000000-8a203209ee26cc9d81b2	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01bi-9427100000-83bbdc724a92bedb9dd9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-007c-0090000000-c072e5e5207b8c910fb0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0036-0590000000-b615c774781c63631475	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-1900000000-2b7cf789bff4868649b5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-016a1ced5998391f910d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-0290000000-f825e5f837e939c27da6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052g-8980000000-5333ae5b5ce67dd5e54d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-993c9e1d7e7cf2f7fc90	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mn-0790000000-ad5581853fcf6bba5c6f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00mn-2920000000-a796fcd75cb858a9a779	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-19de8b5ab0e62272a9e4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007c-0190000000-eab8f030770e8aaaba37	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001m-1930000000-765209de6319e55c489e	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0034881

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013456

KNApSAcK ID

Not Available

Chemspider ID

35013791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751635

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-propanoic acid (MMDBc0033510)

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3D-SDF for #<Metabolite:0x00007fecec00c590>

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3D PDB for #<Metabolite:0x00007fecec00c590>

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3D Structure for #<Metabolite:0x00007fecec00c590>